Isomerization of trioses in acid solutions catalysed by molybdate ions

Königstein, Jozef

doi:10.1135/cccc19781152

Cited by 7 publications

(2 citation statements)

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“…The irreversible conversion of DHA–Gld to MGO follows first-order kinetics according to the work of Grainger et al and was reported to be catalyzed by a broad range of species. Spoehr and Strain provided evidence of catalysis by weak alkalis, including various organic amines [ 90 , 114 ], or a large range of polyvalent anions [ 90 , 94 , 115 ], extensively studied by Riddle and Lorenz [ 116 ]. The latter specifically showed strong catalysis by fructose and glucose phosphate species, which are known to be precursors of DHA and Gld phosphates in metabolism ( Figure 2 ).…”

Section: A Multi-functional Synthesis Tool: Dha’s Broad Range Of Reac...mentioning

confidence: 99%

Dihydroxyacetone: A User Guide for a Challenging Bio-Based Synthon

et al. 2023

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1,3-dihydroxyacetone (DHA) is an underrated bio-based synthon, with a broad range of reactivities. It is produced for the revalorization of glycerol, a major side-product of the growing biodiesel industry. The overwhelming majority of DHA produced worldwide is intended for application as a self-tanning agent in cosmetic formulations. This review provides an overview of the discovery, physical and chemical properties of DHA, and of its industrial production routes from glycerol. Microbial fermentation is the only industrial-scaled route but advances in electrooxidation and aerobic oxidation are also reported. This review focuses on the plurality of reactivities of DHA to help chemists interested in bio-based building blocks see the potential of DHA for this application. The handling of DHA is delicate as it can undergo dimerization as well as isomerization reactions in aqueous solutions at room temperature. DHA can also be involved in further side-reactions, yielding original side-products, as well as compounds of interest. If this peculiar reactivity was harnessed, DHA could help address current sustainability challenges encountered in the synthesis of speciality polymers, ranging from biocompatible polymers to innovative polymers with cutting-edge properties and improved biodegradability.

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Section: A Multi-functional Synthesis Tool: Dha’s Broad Range Of Reac...mentioning

confidence: 99%

Dihydroxyacetone: A User Guide for a Challenging Bio-Based Synthon

et al. 2023

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“…Where MGO in Manuka honey comes from MGO is derived from its parent molecule dihydroxyacetone (DHA) and is converted from DHA to MGO through nonenzymatic Maillard reactions (4). The conversion from DHA to MGO is essentially a non-reversible dehydration reaction which requires both acidic and basic conditions (19). If conditions are only acidic aqueous, then only dehydration of DHA to MGO occurs.…”

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confidence: 99%

Antibacterial Properties of Manuka Honey and the Role of Methylglyoxal

Feng

2023

J Stud Res

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The unique ecosystems of New Zealand have produced a diverse range of honey over the years, with Manuka honey being one of the most renowned. Produced by Western honeybees extracting nectar from Manuka flowers, this monofloral honey has become known for its distinct antibacterial and anti-inflammatory properties. Whilst antibacterial activity in other honey tend to stem from factors such as hydrogen peroxide content, high viscosity, osmotic effect, and acidic pH, the antibacterial activity of Manuka honey is mainly attributed to methylglyoxal (MGO), a dicarbonyl compound which is found in high concentrations in Manuka honey. This review paper will focus on the antibacterial properties of Manuka honey and the role that MGO plays. Understanding the specific chemical mechanisms that of attack on different strains of bacteria by Manuka honey and the role of MGO is crucial to potentially understanding how new drugs or medicines can combat antibacterial resistance to antibiotics.

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New Mechanistic Proposal for Some Heptamolybdate‐Ion‐Catalyzed Isomerizations

Klaić

Raza

Sanković

et al. 1987

Helvetica Chimica Acta

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Heptamolybdate‐ion(HM)‐catalyzed C(2) epimerization of D‐glucose and racemization of D‐glyceraldehyde proceed with comparable rates and activation parameters; HM catalyzes the isomerization of glucal and galactal triacetates as well. For all of the above transformations, a common, new mechanism is proposed that invokes stabilization of 3‐oxa‐allylic cation species by the central Mo(VI) atom.

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Isomerization of trioses in acid solutions catalysed by molybdate ions

Cited by 7 publications

References 0 publications

Dihydroxyacetone: A User Guide for a Challenging Bio-Based Synthon

Dihydroxyacetone: A User Guide for a Challenging Bio-Based Synthon

Antibacterial Properties of Manuka Honey and the Role of Methylglyoxal

New Mechanistic Proposal for Some Heptamolybdate‐Ion‐Catalyzed Isomerizations

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